Line a baking sheet with parchment or wax paper. Melt the orange candy melts in a microwave-safe bowl in 20–30-second intervals, stirring thoroughly after every interval until smooth; add the shortening only if the coating is too thick.

Carefully separate each Oreo, keeping the cream filling attached to one cookie half. Dip the tip of each lollipop stick into the melted orange coating, press it into the cream center, and replace the top cookie.

Let the assembled cookies firm briefly, or chill them for about 5–10 minutes for a more secure pop. Dip each Oreo completely into the orange coating and gently tap the stick against the bowl to remove excess.

Place the coated pops on the lined baking sheet. Before the orange coating sets, add a small green stem or vine detail with green candy melts or green decorating icing if desired.

Allow the coating to harden at room temperature, or refrigerate the pops for 10–15 minutes. Once firm, draw or pipe pumpkin eyes, noses, mouths, and vertical pumpkin lines with black candy melts, icing, or a food-safe edible marker.